The 1998 Daytona 500, the 40th running of the event, was held on February 15 at Daytona International Speedway in Daytona Beach, Florida as the first race of the 1998 NASCAR Winston Cup season. It was memorable in that it marked Dale Earnhardt's only Daytona 500 victory after 19 previous attempts and many heartbreaking finishes. Not only was it Earnhardt's 20th 500 start, but also CBS's 20th consecutive live broadcast of the Daytona 500. Also, his long-awaited Daytona 500 win snapped a 59-race winless streak dating back to Atlanta Motor Speedway in March 1996.

The race was remarkably clean for a restrictor plate race. There were only three cautions - all of which were for minor incidents (as well, there were no accident-related retirements), and there was a pit stop incident involving Dale Jarrett, Jeff Burton and Derrike Cope but no caution was waved. The race was run under the green flag for the first 125 laps. This resulted in it being the second-fastest Daytona 500 ever, behind the 1980 Daytona 500 won by Buddy Baker, and the fastest of the restrictor plate era.